Triacetoxyperiodinane → HCID 86732739, compound

HRID 525872Notes

Reaction equation

HRID 525872 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[C:6](=[O:33])[C:5]([CH2:34][OH:35])=[N:4]1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[C:6](=[O:33])[C:5]([CH:34]=[O:35])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86732738HCID 86732738, compound

Product 1

HCID 86732739HCID 86732739, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-ethyl-3-(hydroxymethyl)-6,7-bis((4-methoxybenzyl)oxy) cinnolin-4(1H)-one (1.6 g, 3.36 mmol) in dichloromethane (DCM) (50 mL) at room temperature was added Dess-Martin periodinane (1.709 g, 4.03 mmol). The white suspension turned into a dark green solution. The reaction was stirred at room temperature for 1 h, treated with sodium bicarbonate solution and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by automatic silica gel column chromatography (Combiflash RF), eluting with ethyl acetate/hexanes (0-100%) to afford 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carbaldehyde (0.9 g, 1.897 mmol, 56.5% yield) as a yellow solid. LCMS: (M+H)+: 475.2

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by automatic silica gel column chromatography (Combiflash RF)
  7. washeluting with ethyl acetate/hexanes (0-100%)

Sources & evidence

ORD record
ord-30c9e5af4b3d4521bafe18404c84683f
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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